


Dean Becomes Triana's Plaything

by squishy_dean



Category: The Venture Bros
Genre: Bondage, Consensual Kink, Dom/sub, Edging, F/M, Masturbation, Teasing, female dom, male sub
Language: English
Status: Completed
Published: 2019-05-23
Updated: 2019-05-23
Packaged: 2020-03-10 02:39:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,582
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18929620
Author URL: https://archiveofourown.org/users/squishy_dean/pseuds/squishy_dean
Summary: Triana catches Dean beating his meat. Amusement ensues.





	Dean Becomes Triana's Plaything

It was the stroke of midnight in the Orpheus household. Hank and Dean took up one of the many guest bedrooms, as Brock and their dad were on another one of their adventures.   
“This is so lame, DeanO! We should be out there fighting bad guys with Pop and Brock. Not cooped up in here reading Hardy Boys!”  
“Yeah. It’s no fun when they leave us behind.” Dean sat up on his bed “Well on the bright side, maybe Triana will stop by!” His face lit up when he said her name.   
“Oh not you and your fake girlfriend again..” The boys were interrupted by Dr. Orpheus making his entrance. His cloak swept across the floor, sending a cold chill into the air. Lightning ripped through the sky, as if signaling his arrival.  
“Who wants some warm milk and cookies?!”  
“Oh boy, do I! Thanks Dr. O!”   
“Sleep tight, boys! And do not let the bed bugs bite….NOR THE DARK MARE, WHO MAY GALLOP INTO YOUR PSYCHE LIKE A SHADOW OF DREAD, INJECTING SORDID DREAMS OF UNIMAGINABLE TORTURE AND DAMNATIONNN!”

Shortly after his cup of warm milk, Hank passed out. But Dean tossed and turned. He just couldn’t stop thinking about the fact that he was in the same house as Triana. What if she got scared of the storm and went to him for comfort? ‘Hold me, Dean’ ‘Don’t be afraid, my darling’. What if she kissed him...with tongue? He felt a tingling in his pants and moved his hand down without thinking.  
'No wait! I can’t do this here.. not at Triana’s house'. He tried to ignore it, but it was no use. Whenever he tried to think of something else, his mind would go back to “...Triana”. After a while, it was starting to get annoying, so he decided he should just touch himself to make it go away. He felt kind of dirty, wary of the bedroom door being slightly open and Hank sleeping close by. He made a point to think of a scenario that would get him off quickly. He thought of Triana in the room with him, undressing down to her underwear and getting into bed beside him. Feeling more relaxed, his eyes closed, and his mouth contorted as these thoughts evolved. He imagined putting his tongue between her teeth and sliding his hand into her underwear. But suddenly, he was interrupted by a sound in the doorway.   
“What are you doing?” It was Triana. Dean screamed and covered his shame. Hank was startled awake.  
“Triana!!”  
“What happened? Intruder??” Hank jumped up, ready for action.  
“Go back to sleep, Hank. Dean was just having a bad dream.”  
“Triana it’s not what you—“  
“Yeah, yeah it’s ok, you don’t have to explain.” With that she continued down the hall.  
“Jeez, what was that?” Hank asked. Dean just buried his head into his pillow and groaned.

Dean was beyond embarrassed. ‘Now she thinks I’m a perverted weirdo! My life is over!’ His thoughts were racing and he could feel himself tear up, but after a few minutes, he felt a hand rest on his back. He flinched and sprang up. It was Triana again.  
“Shh! Don’t wake up Hank.”  
“What are you doing?”  
"I wanna show you something. Just come with me.” Dean tried to continue with more apologies and explanations, but she just put her finger to his lips.   
She walked him down another corridor, passing by old paintings and rusting armor. Dean didn’t stray far from her side, wary the armor might move like someone was still inside.   
“So where are we going?” He asked, trying to cover the fact that he was spooked.  
“My favorite place in this old house.” Lighting struck again, illuminating the great hall and all its dust and cobwebs.   
“This place sure is creepy at night.” Dean said. Triana just smiled at him and shook her head.  
“Here we are!” Two massive doors began to open with a thunderous sound.   
“What is this place?? Golly those are some big doors!”   
“It’s the play room.”  
“The play room? Well that sounds fun! What kind of toys do you have in there?”  
“I’ll show you. Come on.” The two stepped in and let the doors close behind them. The room was dim and dark for the most part, and there were what looked to be torture devices all around. An iron maiden, stocks, the rack, you name it. Machines and tools all meant to either restrain or inflict pain.  
“This doesn’t look like any play room I’ve ever been in.”  
“Well, it’s a different kind of playroom.”   
“You don’t like, kill people in here, do you?”   
“No, Dean,” Triana laughed, "Of course not.” She edged closer to him and gave him a quick kiss on the lips. His body became tense and blushed. Feeling the tingling again, he tried to subtly hide himself.   
“Why.. why did you kiss me?”   
“Because, Dean, I think you’re really cute. And I saw what you were doing in the guest room. I was thinking, I want to help you with...that.” She motioned to him, now obviously trying to hide an erection.   
“I don’t really know what to say.” He couldn’t look at her when he talked.  
“That’s okay.”  
“I’m really embarrassed right now.”  
“Aw.”  
“I really, really like you, Triana, believe me, I think you’re the coolest girl in the whole world! But I don’t want you to see me like this. I think I should just take care of it by myself.”   
“Oh, Dean. What about this, what if we just start the game, and if you don’t like it, we can stop?” Dean pondered for a few seconds.  
“Hmm.. okay.”   
“Wicked! Okay but you’ll have to take your hands off your junk.” She pulled away his hands and he instinctively covered himself again.   
“HEY!”   
“Hey what? You said you’d play. Really, you have nothing to be ashamed of.”   
Dean thought about all his secret fantasies of her. The thoughts he pushed to the way back in his mind. Even though it was daunting and scary, a big, big part of him wanted to experience them for real. He slowly took his hands away. She looked into his eyes and took his hands, “Dean I promise if it gets to be too much we can stop.” He smiled,   
“Okay. I’m ready.”   
“Awesome! You should start by putting on these.” She held out a pair of girly underwear with lace trim.   
“You wanna see me in those??” He looked confused.  
“Well you’re going to play the damsel in distress! I can’t have you wear what you have on now for that, can I?”  
“I guess not…"  
He took off his pajamas and white briefs, switching to the girly pair. “Do you have to look?”  
When he was properly changed, she grabbed him by the wrist and dragged him to a far wall.   
“Ready to be the damsel?”  
“Ready!” She restrained him by the wrists so he’d have to stand with his arms up, and put a metal collar around his neck. He shivered at the cold metal on his skin and squirmed, trying to get comfortable and failing. “Oh wow! It is like a real life dungeon! Well now what? Should I call for help like a real damsel in distress? Help me, oh help me! Where is my prince? My knight in shining armor?!” Triana ignored him and started taking off her clothes. “O-Oh.” Dean’s face grew hot and he looked away. Now she was in her bra and underwear, an image he’d only dreamed of seeing.  
“No, look at me, Dean.” She gripped his chin in her palm and made him face her. By this point he was light headed with lust and extremely hard. He whimpered from embarrassment. Triana got down on her knees and reached out for his dick. Dean flinched, instinctively trying to cover himself again, but the restraints halted his sudden tug. She stopped watched him for a second, contorted, and breathing shallowly, one thigh crossed over the other, still desperately trying to cover himself. He wanted her so bad but was just so nervous about how he’d appear to her. He was just so, so inexperienced.  
He had recited their first kiss in his head countless times. He always imagined they’d go slow and start out with something sweet. And sure, he thought about dirtier scenarios too, but, he never had something quite like this in mind. He wasn’t even completely sure what this was; Except that it was a game, and despite his fear, he was feeling...really good.  
“You really need to relax. I don’t know why you’re so squirmy, I just want to try something, okay?”   
“Triana no!” He whined. But by now she had pulled down his panties. “Aah!”  
“Wow, you really don’t have to be embarrassed. And, you’re breathing pretty heavily, are you okay? Do you need us to stop already?”  
“No we don’t have to stop! I’m just nervous is all. To be honest, no girl has seen me naked yet.”   
“You don’t say."  
She kissed him and slipped her tongue into his mouth, just like he had imagined. He closed his eyes and was getting into the kiss, wishing he could feel her up. Then, he was caught off guard as her hand gripped tight around his dick. He made a noise in response, muffled by her mouth.  
Triana’s mouth went lower, kissing his neck and chest, his flat stomach and hip bones, and even lower... A shockwave went through his body when she put her mouth around his dick. “Trianaaa...” He whined, his wrists straining against the rope. Finally, he was letting go a little more and allowing himself to enjoy it.  
“Is that okay?”   
“That feels so much better than my hand.”   
“Okay, I’ll keep going.” He squealed as she gripped the base of his dick, jerking and sucking on the tip at the same time. His legs starting shaking a little.  
“I feel it, I think I’m going to--”   
“Are you going to cum? Already? God that’s so cute. Okay, hold on.” She stopped what she was doing and stood back up.   
“What?? Where are you going?”   
“This is part of the game.” She unhooked her bra and dropped it to the ground. Dean’s full attention was on her. When he finally looked down, he could see clear liquid leaking from his penis. He bet if she just touched him in that moment he would have came.   
“Oh my god. This is torture!” He moaned.  
“Well yeah, we’re in a torture chamber. Now come on. What do you want?”  
“Y-you know.”  
“Yeah but I want you to say it.”  
“I don’t want to...”   
“If you don’t beg, you won’t get any more.” Dean had never been so turned on. The need for sex was taking over his brain, pushing his usual sensible and cautious nature to the side.   
“I want you! I want you to play with my.. I want you to put it in your mouth again! Please!”  
“Wow, how assertive. Suddenly I’m so hot.” She said in a sarcastic monotone. She took her time walking back over to him. Finally, she knelt down and gave his dick a nice long lick. He arched his head up and closed his eyes, making a desperate sound. He was starting to sweat now. Keeping in mind what she said before, he tried to focus on not cumming, but he knew it would be a huge challenge, especially with her sucking on the tip like that.   
At one point Triana stopped briefly and put her finger in her mouth before going back to playing with him. He was baffled by this but too distracted to care. He felt her hand on his ass which he definitely didn’t mind, but then,  
“AAaH!” He was startled by her finger that strayed a little too far. “Why did you do that??”  
“You might really like how it feels. I won’t even stick it in.”  
“I don’t know…"  
“It’s like a massage, it feels so good, I promise.” He just looked at her, not completely trusting. “I’ll be so gentle, and if you hate it, we can stop, remember?”  
“Ugh... Okay.” He felt humiliated. He’d never thought anyone would touch him there in his life. It felt so invasive, but he really wanted to please Triana, and everything else she had done so far felt really good, even if it hurt a little too. Like those restraints. His arms were starting to fall asleep and he couldn’t really feel his hands anymore. His fingers twitched slightly when he tried to move them.  
Triana put her finger back and started massaging in small circles. Dean shuddered and made a sound like he was in pain.  
“Relax, you’re so tight.”   
He took a deep breath and focused on relaxing. “There, that’s better, isn’t it?" He had to admit, it was starting to feel pretty good. A nice warm, wet feeling. He wondered if this was what having a pussy felt like. He felt light headed again and he sighed deeply, smiling like a fool as she started sucking on him again. But then, she stuck her finger in a little, snapping him out of the bliss and making him scream.  
“You’re so noisy!”  
“You didn’t warn me!!”  
“I really like the noises you make though, will you do it again if I—“ She stuck her finger in again.  
“AAAaah!” He contorted his body away from her. “What the hell!”  
“I’m sorry,” she couldn’t stop smiling.  
“No you aren’t.”  
“Your sounds just make me so wet.”  
“Huh?”  
“Here, I’ll just untie you now, I bet those restraints are getting really uncomfortable.”  
He felt his heart leap out of his chest. Since they got started, he’d wanted nothing but to touch her. He looked up, watching her loosen the slack on the knots. He really liked how her boobs looked at that angle.   
When his arms were freed they felt felt heavy but also like they’d been drained of blood.   
“I can’t really feel my arms.”  
“Yeah that will wear off.”  
“Can I kiss you again?”  
“We can do more than that, hun.” Without even thinking, Dean kissed Triana, putting his fingers through her hair. She pressed herself into him, wrapping a leg around him and putting her arms around his shoulders. Dean couldn’t resist moving his hands lower to feel up her boobs. He’d always wondered what they’d feel like. Triana then broke the embrace and looked into his eyes. “Dean, can you do something for me?”   
“Anything.”  
“Get down on the ground for me.”   
Obliging, he laid down on his back, despite the cold floor giving him goosebumps.”Are you cold?”  
“Yeah, a little.”  
“It’s okay, baby. I’ll warm you up.” Triana threw her underwear to the side and straddled him, making him blush. When she slipped him inside of her, his eyes rolled back and he felt completely euphoric. 

Dean opened his eyes. He was back in Dr. Orpheus’s guest room. The sun was only just beginning to come up. He groaned and rubbed his eyes, feeling like he had slept for a solid month. Then, noticing how wet he felt, he looked in his underwear and saw the most cum he’d ever made in there. Seeing it made him remember the dream he just had, and his heart dropped to his stomach. He suddenly felt wide awake.  
“What the fuck was that??"


End file.
